Enantio- and diastereoselective synthesis of spiropyrazolones via an organocatalytic [1+2+3] multicomponent reaction

被引：17

作者：

Ji, Yan-Ling ^{[1
]}

Li, He-Ping ^{[1
]}

Ai, Yue-Yan ^{[1
]}

Li, Guo ^{[1
]}

He, Xiang-Hong ^{[1
]}

Huang, Wei ^{[1
]}

Huang, Rui-Zhen ^{[2
]}

Han, Bo ^{[1
]}

机构：

[1] Chengdu Univ Tradit Chinese Med, Sch Pharm, State Key Lab Southwestern Chinese Med Resources, Chengdu 611137, Sichuan, Peoples R China

[2] Hosp Chengdu Univ Tradit Chinese Med, Chengdu 610072, Sichuan, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 41期

基金：

中国国家自然科学基金;

关键词：

3+3 ANNULATION REACTION; ASYMMETRIC-SYNTHESIS; DIASTEREODIVERGENT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREOGENIC CENTERS; CONSTRUCTION; CASCADE; QUATERNARY; CATALYSIS; CYCLOADDITION;

D O I：

10.1039/c9ob01927h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric catalytic multicomponent reaction of malononitrile, benzaldehyde, and alpha-arylidene pyrazolinones to produce spiropyrazolones has been reported. The [1 + 2 + 3] multicomponent reaction was catalyzed by chiral cinchona alkaloids to provide spiropyrazolones in high yields, with excellent enantioselectivities and good diastereoselectivities. We also performed control experiments and proposed a plausible catalytic cycle based on the observed experimental results to explain the reaction process and stereoselectivity of the asymmetric multicomponent reaction.

引用

页码：9217 / 9225

页数：9

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